Holiday rentals with outdoor seating in Charlottesville

5 out of 5 average rating, 210 reviews

A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.

Cottage in Afton

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

Guesthouse in Charlottesville

A light-filled living area features large windows that overlook a serene outdoor space. A cozy sofa with cushions is positioned beside a standing lamp, while a decorative rug lies on the polished wooden floor. A potted plant adds a touch of greenery to the inviting atmosphere.

5 out of 5 average rating, 120 reviews

Honey House-modern loft near UVA/Monticello

Modern loft style 800sqft guesthouse. Lots of light and privacy in a quiet neighborhood, just 7-10 minutes to Scott Stadium/UVA/restaurants/downtown mall and Thomas Jefferson’s Monticello. Central to many wineries/breweries. You are in nature but close to everything Charlottesville. With a comfortable Queen size bed, and sleeping cot available if necessary. It is clean, comfortable and spacious. A great place to unwind for a good night’s sleep and sweet dreams. (discount apply to weekly/monthly)

4.97 out of 5 average rating, 231 reviews

A bright living area features a striped sofa adorned with green and gold cushions. A wooden coffee table sits in the center, complemented by a soft armchair nearby. Natural light filters through two windows, casting a warm glow on the decor, including framed artwork and a large flat-screen TV.

Apartment in Belmont

Belmont BnB ~ 2BR/1BA ~ Comfort & Convenience

Welcome to our well-appointed, centrally located 2 BR/1BA apartment! This cozy spot, with comfy queen beds, full kitchen, and cottage garden is a perfect homebase to relax in after a day of exploring. Set out on foot to: • Belmont Park (2 blocks) • Belmont Restaurants (15 min) • The Rivanna Trail (5 min) • The Downtown Mall (20 min) Short drives to Monticello (< 4 mi), grocery stores (1-2 mi), and UVA (2 mi). Your hosts are readily available in the above apartment should you need anything!

Guesthouse in Charlottesville

A covered front porch features a mix of seating options, including wicker chairs and a small table. Hanging planters add greenery, while potted plants contribute to the inviting setting. The porch overlooks mature landscaping, providing a serene outdoor environment.

5 out of 5 average rating, 102 reviews

Historic HomeTract Cottage UVA/Charlottesville/Ivy

Hometract Cottage is a historic one bedroom home (NRHP, circa 1800) centrally located 15 minutes or less from Charlottesville, UVA, Crozet, Monticello, wineries and more. The cottage features ensuite bath, fully stocked kitchen, living/workspace with comfortable sleeper sofa, mature landscaping for privacy, and covered front porch. Hometract is a quiet 3-acre property with terraced garden views. Visit our chicken coop, relax in the hammock, or walk to the garden shop or Duner's restaurant.

Guest suite in Waynesboro

A spacious front porch is adorned with vibrant flowers in various shades, creating a welcoming environment. Comfortable seating is arranged to invite relaxation, while lush greenery provides an enhanced view of the surrounding area. A patterned outdoor rug complements the serene setting.

4.99 out of 5 average rating, 342 reviews

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home in the City of Waynesboro is just a short drive from the Blue Ridge Parkway. Modern amenities, light complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is yours to enjoy including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

4.88 out of 5 average rating, 604 reviews

A gourmet kitchen is highlighted with a stainless steel gas range and sleek countertops, seamlessly connecting to an open living space. Warm wooden floors enhance the visual appeal, while recessed lighting creates a bright and inviting atmosphere.

Apartment in Belmont

Designer Belmont Apartment! Close to everything!

Renovated luxury apartment with private entrance. Gourmet kitchen for entertaining or having a relaxing weekend away! We are steps away from Belmont with some of the best rated restaurants in Cville. Also, you are a 5-10 minute walk to The Historic Downtown Mall. Great OPEN space to come back relax with large deck and garden. The space: - Designer/Luxury Apartment - Gourmet Kitchen w/ Gas Range - Quiet neighborhood - Parking - Walking distance to DTM - Sleeps 4 - Soundproofed - Washer & Dryer

4.97 out of 5 average rating, 360 reviews

The image features a charming two-story home surrounded by lush greenery and flowering trees. A circular driveway leads to the entrance, with manicured lawns enhancing the exterior. The backdrop includes rolling hills and bright blue skies, creating a serene and inviting setting.

Home in North Garden

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

4.99 out of 5 average rating, 216 reviews

The outdoor firepit area is surrounded by wooden seating and log stump tables. Two wooden structures flank the space, providing a unique aesthetic. The treehouse sits elevated in the background, with trees displaying autumn foliage creating a vibrant backdrop.

Treehouse in Verona

The Laurel Hill Treehouse

Fully immerse yourself in nature in this serene Scandinavian-inspired woodland retreat, perfect for a couple's getaway. The treehouse is perfectly nestled amongst the trees, offering a chance to unwind while enjoying the beautiful views of nature. Just imagine yourself relaxing on the wrap around porch, soaking in the hot tub, cooling off in the creek, & cozying up to a crackling fire. We invite you to unwind, reconnect with nature & create cherished memories in this tranquil hideaway.

Apartment in North Downtown

The living room features two couches, one dark leather and one brown, arranged around a central coffee table on an area rug. A flat-screen TV is mounted on the wall, and large windows allow natural light to fill the space, enhancing the contemporary feel.

4.85 out of 5 average rating, 465 reviews

*Large Private Apartment In Downtown Cville*

The main floor of this house has a private entrance and a nice, beautiful walk to the Historic Downtown Mall, near hit restaurants, arts, live music & shopping. Very quiet neighborhood. 2 bedrooms with a large living room, dining room, and full kitchen make this a great spot for 1-4 guests. Your own apartment for your Charlottesville stay! 2 outdoor porches give great spots to relax. Decorated throughout with the work of great local artists. Super-Fast WiFi, all kitchen necessities.

4.96 out of 5 average rating, 116 reviews

A rustic cottage exterior is showcased, featuring weathered wood siding and a steeply pitched roof adorned with a central peaked window. Flanking the entrance are symmetrical decorative elements and manicured greenery. The surrounding landscape includes seasonal foliage, enhancing the natural setting.

Cabin in Charlottesville

Ivy Rose Cottage nestled b/t Cville & Vineyards

The Ivy Rose Cottage bestows an exceptional ambiance that will captivate your heart. Whisk yourself away to this two bedroom cottage located in Ivy halfway between the Shenandoah Park/Brewery Trail and Charlottesville, home of UVA. The Ivy Rose Cottage, designed and handbuilt by the hosts, is an enchanting mix of cypress, timber frame, copper trellis work, pergolas and other architectural treasures. Fully equipped kitchen and a washer/dryer for those lengthier stay conveniences.

4.98 out of 5 average rating, 127 reviews

A welcoming exterior of a curved house is presented, featuring a light stone pathway leading to a front porch. Two white rocking chairs are positioned in front, with decorative planters filled with greenery on either side. The backdrop consists of lush trees and a blue sky.

Home in Charlottesville

Unit 1_Expansive Luxury Suite for up to 4 Persons

Take a journey to Albemarle County and experience historical sites and luxurious accommodations. Sonsak is uniquely situated on the Thomas Jefferson Parkway; nears area's most celebrated landmarks, including Monticello - Home of Thomas Jefferson, directly across Michie Tavern and near Ash Lawn - Home of James Monroe, Carter Mountain Orchard and numerous Vineyards. Embark on a 'Journey Through Hallowed Ground', an unforgettable experience that's packed with history and beauty.

5 out of 5 average rating, 179 reviews

The kitchen features white cabinetry with glass-front doors and a herringbone backsplash. A farmhouse sink sits below a window, complemented by modern appliances, including a gas stove and a stainless-steel dishwasher. Natural light streams in, highlighting the spacious countertop area.

Home in Lewis Mountain

Cavalier Cottage-3 BR/Bath, Calm Amid UVA Grounds

Fully-updated, custom home in premier location. Warm hardwoods, lots of light, comfortable sofas & beds, easy check-in -- we strive to make your stay restful and refreshing. Nestled between Scott Stadium & JPJ, O'Hill & the Rotunda, wine country & the downtown mall, you could not be closer to the action yet in a quiet, residential neighborhood. The perfect place for any & all Cville/UVA events, work trips, reunions, weddings, family vacations, college visits, etc.

Popular amenities for Charlottesville outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.92 out of 5 average rating, 119 reviews

A newly renovated two-story home is showcased with a dark exterior and inviting front porch. Comfortable seating arrangements are positioned under the covered area, and a well-kept lawn, flanked by shrubs, adds to the exterior appeal.

Home in Belmont

Montrose Manor- In the heart of Belmont!

4.98 out of 5 average rating, 109 reviews

A sunroom is filled with natural light, featuring a dark sofa adorned with decorative pillows. A small side table with a lamp is positioned beside the couch. A comfortable chair complements the seating area, while large windows showcase lush greenery outside.

Home in Charlottesville

The Venable - A Gorgeous Home in the Heart of UVA

4.94 out of 5 average rating, 316 reviews

Home in Mount Crawford

HOT TUB, WIFI, Near Buc-ee’s, I81, yet secluded!

4.97 out of 5 average rating, 157 reviews

The exterior of a two-story colonial-style house is visible, showcasing a well-maintained front yard with mature greenery. A gravel driveway leads to a covered parking area. Bright blue skies and scattered clouds frame the scene, highlighting the peaceful, natural surroundings.

Home in Charlottesville

Wakefield Ct | Private Parking spots | Fast WiFi

4.98 out of 5 average rating, 160 reviews

A modern cabin-style home is nestled among tall trees, showcasing a sleek black exterior. A spacious screened-in porch is visible, supported by a deck with steps leading down to a gravel path. Large windows enhance the connection with the natural surroundings.

Home in Orange

Hidden Haven

4.95 out of 5 average rating, 416 reviews

A charming Craftsman-style cottage is presented, featuring a welcoming front porch with rocking chairs. A lush green lawn surrounds the home, complemented by mature trees. The exterior showcases a soft grey color, and the entrance is marked by a wooden door with house number 536.

Home in Woolen Mills

High Note | Parking X3 | Sleeps 6 | Rivanna Access

4.97 out of 5 average rating, 133 reviews

A modern house is nestled within a lush forest, partially hidden by tall trees. Large glass windows reflect the surrounding greenery, while a spacious deck extends from the structure, offering a view of the forest floor. The entrance is accessed via a gravel pathway.

Home in Dyke

Moss Vineyards Lodging

5 out of 5 average rating, 109 reviews

A comfortable living area features a gray sofa adorned with patterned throw pillows. A modern table sits in front, displaying a potted plant and a decorative tray. Colorful artwork hangs above the sofa, while a lamp provides soft lighting in the corner.

Home in Keswick

One Level Living at Shadwell Terrace

Apartment rentals with outdoor seating

5 out of 5 average rating, 171 reviews

A welcoming entryway is presented with floral wallpaper and green wainscoting. A small armchair, paired with a decorative lamp and side table, creates a cozy reading nook. Artwork is hung on the walls, and a door leading to the outside is visible at the end of the hallway.

Apartment in Staunton

Queen City Hideaway

Apartment in North Downtown

A living room featuring a classic tiled fireplace with an electric insert, surrounded by dark wooden paneling. A cozy red trunk and a wooden chair complement the space, while a patterned rug adds warmth. Glass display cabinets showcase decorative items, enhancing a historic ambiance.

4.91 out of 5 average rating, 397 reviews

UVA, Downtown Mall, Historic Area

Apartment in Charlottesville

A well-lit living area features a comfortable sofa, two patterned chairs, and a coffee table. A television is placed on a white entertainment unit, while soft lighting from nearby lamps creates a cozy ambiance. Light wood flooring complements the neutral color scheme.

4.83 out of 5 average rating, 234 reviews

Clean, central, spacious, private - UVA/Downtown

Apartment in Wintergreen Resort

A table set for two features a bottle of sparkling beverage and two glasses, accompanied by an elegant plate of appetizers. The backdrop showcases expansive mountain views under a bright sky, enhancing the serene atmosphere of the outdoor dining area.

4.97 out of 5 average rating, 105 reviews

Mountain View Nest

4.98 out of 5 average rating, 115 reviews

A cozy living area is equipped with a vibrant yellow armchair and a light gray sectional sofa. A large screen TV is mounted on the wall, and natural light enters through a window adorned with white curtains. A round wooden coffee table sits on a patterned area rug.

Apartment in Culpeper

Red Fox Retreat

4.98 out of 5 average rating, 205 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

4.88 out of 5 average rating, 684 reviews

A single-story brick house is shown, featuring a sloping roof and a well-maintained front lawn. Tall trees and greenery frame the property, contributing to a peaceful outdoor environment. A clear pathway leads to the entrance, reflecting the inviting nature of the home.

Apartment in Greenbrier

Cozy 1BD FULL PRIVATE APT in Charlottesville, VA

4.91 out of 5 average rating, 260 reviews

A private hot tub is positioned on a wooden deck, inviting relaxation. The exterior of a two-story building is visible in the background, featuring a well-maintained lawn and a staircase leading to a covered porch. Soft lighting illuminates the outdoor seating area.

Apartment in Madison

The Studio at Dark Run Retreat

Condo rentals with outdoor seating

A cozy living room is presented, featuring two plush leather sofas, a coffee table, and a fireplace. Natural light enters through large windows, and decorative accents enhance the warm ambiance. A flat-screen TV sits on a stand, completing the inviting space.

4.98 out of 5 average rating, 192 reviews

Cozy getaway with heated floors

An inviting living space features a comfortable sectional sofa arranged around a round coffee table, complemented by a cozy rug. A gas fireplace is framed by white paneling, and large windows provide ample natural light while showcasing views of the surrounding landscape.

4.95 out of 5 average rating, 140 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.

4.95 out of 5 average rating, 326 reviews

Five Minute Walk to Everything!

A cozy living area features a teal sofa with a yellow accent pillow and a light wood coffee table. The kitchen is adjacent, showcasing modern appliances. Stairs lead to the loft bedroom. Artwork hangs on the wall, and natural light enters through high windows.

4.97 out of 5 average rating, 144 reviews

Ski-In Ski-Out ~ Mtn Views ~ King Suite

4.9 out of 5 average rating, 141 reviews

Panoramic Peak: Wintergreen Condo with Views

A comfortable living area features a spacious gray sofa and a wooden coffee table, positioned on a patterned rug. Light from a nearby lamp and large sliding doors illuminates the space, which offers views of the outdoors. A cozy accent chair completes the inviting setup.

4.95 out of 5 average rating, 217 reviews

New Construction! 1 Bed/2 Bath, pet friendly

A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.

4.97 out of 5 average rating, 154 reviews

2-min drive from slopes, stair-free/free firewood!

A glass of white wine is positioned in the foreground, capturing the warm hues of a sunset. The sun's golden rays reflect off the wine, while silhouettes of trees and distant mountains create a tranquil backdrop in the evening sky.